TWI283661B - Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes - Google Patents
Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes Download PDFInfo
- Publication number
- TWI283661B TWI283661B TW091108939A TW91108939A TWI283661B TW I283661 B TWI283661 B TW I283661B TW 091108939 A TW091108939 A TW 091108939A TW 91108939 A TW91108939 A TW 91108939A TW I283661 B TWI283661 B TW I283661B
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- Prior art keywords
- oxygen
- catalyst
- source
- oxide
- metal oxide
- Prior art date
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- -1 alkylene glycols Chemical class 0.000 title claims abstract description 26
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 20
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 title abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title description 24
- 238000003786 synthesis reaction Methods 0.000 title description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 80
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000001301 oxygen Substances 0.000 claims abstract description 74
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 74
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 60
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 37
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 21
- 230000003647 oxidation Effects 0.000 claims abstract description 20
- 239000000376 reactant Substances 0.000 claims abstract description 18
- 230000003197 catalytic effect Effects 0.000 claims abstract description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 105
- 238000006243 chemical reaction Methods 0.000 claims description 46
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 39
- 239000002184 metal Substances 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 26
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052742 iron Inorganic materials 0.000 claims description 7
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052758 niobium Inorganic materials 0.000 claims description 6
- 239000010955 niobium Substances 0.000 claims description 6
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 3
- 239000011133 lead Substances 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910000398 iron phosphate Inorganic materials 0.000 claims description 2
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical group [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 claims description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 2
- 241000282376 Panthera tigris Species 0.000 claims 1
- 241001062472 Stokellia anisodon Species 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 150000002910 rare earth metals Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000002699 waste material Substances 0.000 claims 1
- 230000036961 partial effect Effects 0.000 abstract description 12
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 10
- 238000006356 dehydrogenation reaction Methods 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 238000006735 epoxidation reaction Methods 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 239000010457 zeolite Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000005906 dihydroxylation reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 230000037361 pathway Effects 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000002808 molecular sieve Substances 0.000 description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 229910021536 Zeolite Inorganic materials 0.000 description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910000420 cerium oxide Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000001272 nitrous oxide Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- 229910017119 AlPO Inorganic materials 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KFVPJMZRRXCXAO-UHFFFAOYSA-N [He].[O] Chemical compound [He].[O] KFVPJMZRRXCXAO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- DKQVJMREABFYNT-UHFFFAOYSA-N ethene Chemical group C=C.C=C DKQVJMREABFYNT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZKEYULQFFYBZBG-UHFFFAOYSA-N lanthanum carbide Chemical compound [La].[C-]#[C] ZKEYULQFFYBZBG-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- NFFIWVVINABMKP-UHFFFAOYSA-N methylidynetantalum Chemical compound [Ta]#C NFFIWVVINABMKP-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/22—Synthesis of the oxirane ring by oxidation of saturated compounds with air or molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/846,642 US6765101B1 (en) | 2001-05-01 | 2001-05-01 | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI283661B true TWI283661B (en) | 2007-07-11 |
Family
ID=25298507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091108939A TWI283661B (en) | 2001-05-01 | 2002-04-30 | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6765101B1 (https=) |
| EP (1) | EP1387834A1 (https=) |
| JP (1) | JP2004531542A (https=) |
| KR (1) | KR100885127B1 (https=) |
| CN (1) | CN1290836C (https=) |
| AR (1) | AR033294A1 (https=) |
| AU (1) | AU2002309587B2 (https=) |
| BR (1) | BR0209318A (https=) |
| CA (1) | CA2442094A1 (https=) |
| MX (1) | MXPA03010008A (https=) |
| MY (1) | MY141792A (https=) |
| RU (1) | RU2003134645A (https=) |
| TW (1) | TWI283661B (https=) |
| WO (1) | WO2002088102A1 (https=) |
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| US6667409B2 (en) * | 2001-09-27 | 2003-12-23 | Praxair Technology, Inc. | Process and apparatus for integrating an alkene derivative process with an ethylene process |
| NZ533175A (en) * | 2001-11-29 | 2006-03-31 | Wisconsin Alumni Res Found | Low-temperature hydrogen production from oxygenated hydrocarbons |
| CA2634712C (en) * | 2005-12-21 | 2015-11-24 | Virent Energy Systems, Inc. | Catalysts and methods for reforming oxygenated compounds |
| ES2547913T3 (es) | 2006-05-08 | 2015-10-09 | Virent, Inc. | Métodos para generar polioles |
| US7595410B2 (en) * | 2006-07-18 | 2009-09-29 | Lyondell Chemical Technology, L.P. | Direct epoxidation process using improved catalyst composition |
| US20080076946A1 (en) * | 2006-09-22 | 2008-03-27 | Sumitomo Chemical Company, Limited | Process for producing cycloalkanol and/or cycloalkanone |
| AU2007353527B2 (en) * | 2006-12-20 | 2012-12-20 | Virent, Inc. | Reactor system for producing gaseous products |
| RU2472840C2 (ru) | 2007-03-08 | 2013-01-20 | Вайрент, Инк. | Синтез жидкого топлива и химических реактивов из кислородсодержащих углеводородов |
| FR2913974A1 (fr) * | 2007-03-19 | 2008-09-26 | Arkema France | Procede de vaporisation de glycerol |
| ATE482942T1 (de) * | 2007-04-05 | 2010-10-15 | Dow Global Technologies Inc | Integriertes hydrooxidierungsverfahren mit abtrennung eines olefinoxidproduktstroms |
| AR066574A1 (es) * | 2007-05-18 | 2009-08-26 | Shell Int Research | Un sistema reactor, un proceso de produccion de oxido de olefina 1,2-diol 1,2-diol eter , 1,2-carbonato o alcanolamina |
| US20090292132A1 (en) * | 2007-05-18 | 2009-11-26 | Wayne Errol Evans | Reactor system and process for reacting a feed |
| US9144765B2 (en) | 2007-05-18 | 2015-09-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
| EP2285795B1 (en) * | 2008-05-15 | 2017-03-22 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of alkylene carbonate and/or alkylene glycol |
| CA2724084A1 (en) | 2008-05-15 | 2009-11-19 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an alkylene carbonate and an alkylene glycol |
| DE102008025835A1 (de) * | 2008-05-29 | 2009-12-03 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Ethylenoxid |
| MX2011002059A (es) * | 2008-08-27 | 2011-05-10 | Virent Energy Systems Inc | Sintesis de combustibles liquidos provenientes de biomasa. |
| US8697924B2 (en) * | 2008-09-05 | 2014-04-15 | Shell Oil Company | Liquid fuel compositions |
| EP2204236A1 (en) * | 2008-12-19 | 2010-07-07 | Total Petrochemicals Research Feluy | Catalyst and process for hydrogenation of hydrocarbon feedstocks |
| EP2204235A1 (en) * | 2008-12-19 | 2010-07-07 | Total Petrochemicals Research Feluy | Catalyst and process for selective hydrogenation of alkynes and dienes |
| EP2448675A2 (en) * | 2009-06-30 | 2012-05-09 | Virent, Inc. | Process and reactor systems for converting sugars and sugar alcohols |
| DE102009038398A1 (de) * | 2009-08-24 | 2011-03-03 | Uhde Gmbh | Verfahren und Vorrichtung zur Herstellung von Alkylenoxiden und von Alkylenglykolen |
| US20110152547A1 (en) * | 2009-12-17 | 2011-06-23 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| US9447347B2 (en) | 2009-12-31 | 2016-09-20 | Shell Oil Company | Biofuels via hydrogenolysis-condensation |
| US9303226B2 (en) | 2009-12-31 | 2016-04-05 | Shell Oil Company | Direct aqueous phase reforming of bio-based feedstocks |
| AU2011253083B2 (en) | 2010-05-12 | 2014-08-21 | Shell Internationale Research Maatschappij B.V. | Process including hydrogenolysis of biomass followed by dehydrogenation and aldol condensation to produce alkanes |
| US9428704B2 (en) | 2010-05-12 | 2016-08-30 | Shell Oil Company | Direct aqueous phase reforming and aldol condensation to form bio-based fuels |
| WO2012005824A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| BR112013000649A2 (pt) | 2010-07-09 | 2016-05-31 | Sumitomo Chemical Co | processo para a produção de óxido de olefina |
| JP2013505997A (ja) * | 2010-07-09 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| JP2013506000A (ja) * | 2010-07-09 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| WO2012005825A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012005823A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012009055A1 (en) * | 2010-07-10 | 2012-01-19 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012009052A1 (en) * | 2010-07-10 | 2012-01-19 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2013505996A (ja) * | 2010-07-10 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| CN102304020A (zh) * | 2010-12-01 | 2012-01-04 | 湖南大乘医药化工有限公司 | 采用分子筛吸附2，3二甲基-2-丁烯合成频那醇的方法 |
| WO2012094120A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012094121A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012094123A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| EP2661323A4 (en) | 2011-01-05 | 2017-02-08 | Sumitomo Chemical Company Limited | Process for producing olefin oxide |
| WO2012094119A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012102918A1 (en) * | 2011-01-24 | 2012-08-02 | Sumitomo Chemical Company, Limited | Direct conversion of olefin to olefin oxide by molecular oxygen |
| CN103288781B (zh) * | 2012-02-29 | 2015-04-29 | 中国石油化工股份有限公司 | 一种制备环氧氯丙烷的方法 |
| CN103288779B (zh) * | 2012-02-29 | 2015-04-29 | 中国石油化工股份有限公司 | 一种烯丙醇氧化的方法 |
| AP2014008114A0 (en) * | 2012-05-09 | 2014-12-31 | Stranded Solutions Llc | Method of making oxygenates from a non-catalytic chemical reaction |
| CN103570493A (zh) * | 2013-10-31 | 2014-02-12 | 江苏紫奇化工科技有限公司 | 固载型杂多酸相转移催化氧化合成1,2-邻二醇的方法 |
| CA3065667A1 (en) * | 2017-06-23 | 2018-12-27 | Haldor Topsoe A/S | A process for oxidation of a lower alkene at low temperatures in ammonia-containing gas mixtures |
| GB201713951D0 (en) * | 2017-08-31 | 2017-10-18 | Cambridge Entpr Ltd | A catalytic composite and a method of use thereof |
| US10385032B1 (en) * | 2018-07-06 | 2019-08-20 | Uchicago Argonne, Llc | Selective oxidation of propane to propylene oxide |
| CN110590713B (zh) * | 2019-09-25 | 2023-04-07 | 江苏宏邦化工科技有限公司 | 一种环氧苯乙烷的合成方法 |
| US20230312433A1 (en) * | 2022-02-11 | 2023-10-05 | ExxonMobil Technology and Engineering Company | Selective isobutane oxidation to tert-butanol in the presence of cubane clusters catalyst |
| CN117504927B (zh) * | 2023-11-10 | 2025-04-29 | 江西师范大学 | 一种负载型Ti-MWW分子筛与金属氧化物的复合催化剂及其制备与应用 |
| CN120502333B (zh) * | 2025-07-17 | 2025-09-16 | 潍坊学院 | MoO3-Cu2O-WO3/Mn2O3催化剂及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2238474A (en) | 1941-04-15 | Process for making olefin oxides | ||
| US2178454A (en) | 1939-10-31 | Production of olefin oxides | ||
| US2125333A (en) | 1937-05-08 | 1938-08-02 | Production of olefine oxides | |
| US2437930A (en) | 1943-08-28 | 1948-03-16 | Shell Dev | Production and recovery of olefin oxides |
| US3350422A (en) | 1966-02-01 | 1967-10-31 | Halcon International Inc | Catalytic epoxidation of an olefinically unsaturated compound using an organic hydroperoxide as an epoxidizing agent |
| US3987069A (en) | 1971-08-09 | 1976-10-19 | Petro-Tex Chemical Corporation | Preparation of oxirane compounds by autoxidation |
| US4130570A (en) | 1973-10-19 | 1978-12-19 | Boreskov Georgy K | Method of producing ethylene oxide |
| US4390739A (en) | 1981-10-09 | 1983-06-28 | Exxon Research & Engineering Co. | Hydroxylation of olefins |
| ATE19054T1 (de) | 1981-10-09 | 1986-04-15 | Exxon Research Engineering Co | Verfahren zur hydroxylierung von olefinen mit osmium-halogen-verbindung enthaltendem katalysator. |
| US4413151A (en) | 1982-07-14 | 1983-11-01 | Exxon Research & Engineering Co. | Process for hydroxylating olefins using a supported osmium catalyst |
| GB2129800B (en) | 1982-11-12 | 1986-04-23 | Exxon Research Engineering Co | Process for hydroxylating olefins using an osmium oxide catalyst and sodium hydroxide co-catalyst |
| US4508927A (en) * | 1983-08-02 | 1985-04-02 | The Halcon Sd Group, Inc. | Preparation of glycols from ethylene oxide |
| US4496778A (en) | 1983-10-03 | 1985-01-29 | Exxon Research & Engineering Co. | Process for the hydroxylation of olefins using molecular oxygen, an osmium containing catalyst, a copper Co-catalyst, and an aromatic amine based promoter |
| US4990632A (en) | 1988-03-23 | 1991-02-05 | The Boc Group, Inc. | Process for the production of oxides |
| US5008412A (en) | 1988-07-06 | 1991-04-16 | The Boc Group, Inc. | Process for the production of oxides |
| US5008414A (en) | 1988-12-08 | 1991-04-16 | The Boc Group, Inc. | Process for the production of oxides |
| US5043461A (en) | 1989-01-30 | 1991-08-27 | The Boc Group, Inc. | Process for the production of oxides |
| US5262547A (en) | 1990-10-31 | 1993-11-16 | The Boc Group, Inc. | Process for the production of petrochemicals |
| US5344946A (en) | 1991-04-09 | 1994-09-06 | Solvay Interox Gmbh | Process for the preparation of vicinal diols and/or epoxides |
| WO1998019983A1 (en) | 1996-11-08 | 1998-05-14 | Union Carbide Chemicals & Plastics Technology Corporation | Functionalization of hydrocarbyl-containing compounds |
| DE69731363T2 (de) | 1996-12-25 | 2005-12-22 | Agency Of Industrial Science And Technology | Verfahren zur Epoxid-Herstellung und Katalysator für die Verwendung darin |
| US6156938A (en) | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
-
2001
- 2001-05-01 US US09/846,642 patent/US6765101B1/en not_active Expired - Lifetime
-
2002
- 2002-04-18 WO PCT/US2002/012526 patent/WO2002088102A1/en not_active Ceased
- 2002-04-18 MX MXPA03010008A patent/MXPA03010008A/es active IP Right Grant
- 2002-04-18 AU AU2002309587A patent/AU2002309587B2/en not_active Ceased
- 2002-04-18 KR KR1020037014261A patent/KR100885127B1/ko not_active Expired - Fee Related
- 2002-04-18 CN CNB028093054A patent/CN1290836C/zh not_active Expired - Fee Related
- 2002-04-18 RU RU2003134645/04A patent/RU2003134645A/ru unknown
- 2002-04-18 JP JP2002585404A patent/JP2004531542A/ja active Pending
- 2002-04-18 EP EP02736594A patent/EP1387834A1/en not_active Withdrawn
- 2002-04-18 BR BR0209318-9A patent/BR0209318A/pt not_active IP Right Cessation
- 2002-04-18 CA CA002442094A patent/CA2442094A1/en not_active Abandoned
- 2002-04-29 MY MYPI20021550A patent/MY141792A/en unknown
- 2002-04-30 AR ARP020101596A patent/AR033294A1/es unknown
- 2002-04-30 TW TW091108939A patent/TWI283661B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| AR033294A1 (es) | 2003-12-10 |
| CN1290836C (zh) | 2006-12-20 |
| BR0209318A (pt) | 2004-07-20 |
| CA2442094A1 (en) | 2002-11-07 |
| MXPA03010008A (es) | 2004-06-30 |
| AU2002309587B2 (en) | 2007-09-20 |
| RU2003134645A (ru) | 2005-03-27 |
| KR20040015232A (ko) | 2004-02-18 |
| MY141792A (en) | 2010-06-30 |
| WO2002088102A1 (en) | 2002-11-07 |
| KR100885127B1 (ko) | 2009-02-23 |
| EP1387834A1 (en) | 2004-02-11 |
| HK1066802A1 (en) | 2005-04-01 |
| JP2004531542A (ja) | 2004-10-14 |
| CN1507438A (zh) | 2004-06-23 |
| US6765101B1 (en) | 2004-07-20 |
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